It then curves north along Indian Lake Road to another property line which it then follows west, at the district's northernmost corner.

The boundary turns to the south along this line after roughly 1,200 feet (370 m), then returns to its due-west heading for another half-mile, crossing the rail trail and Mill Road at their junction.

What would become Coleman Station took a long time for Europeans to settle due to land disputes between the colonies of New York and Connecticut.

In the early 19th century farming finally developed, moving from a diverse pre-industrial agriculture to a more specialized focus on milk production after the railroad and industrialization.

Newcomers to the region saw its historic value and fought a precedent-setting court battle in the last years of the century to publicly recognize and preserve it.

Tradition has it that the area, like much of the Harlem Valley in eastern Dutchess County, was thoroughly cleared and cultivated by Native Americans before European settlers arrived.

[1] The agreement allowed for Connecticut landowners to continue to hold title in the Oblong, in order that they would have an incentive to pay for an overdue survey of the land.

[1] The oldest surviving buildings in the district, the farmhouse and barn at the Wheeler-Collins Farm on Coleman Station Road, have been dated to about 1771, shortly after land-transaction records start being kept regularly.

They supplemented their farm income with the extraction of raw materials for early industrial production like iron, limestone and peat, from nearby hillsides and bogs.

[1] The 1870 census for the first time recorded fluid milk production, with the Coleman Station farmers' herds putting out 10,000–15,000 US gallons (38–57 m3) annually.

Farms still produced their own butter in quantity, but left cheese production and its enormous fluid milk requirements to the processing plant.

[1] With the coming of the railroad, local entrepreneur Amasa Coleman lobbied for the construction of the station that would take its name from him and give it to the area.

He and Oliver Barrett convinced what was by then the New York Central that a separate stop less than two miles (3 km) north of its Sharon station would help it better serve both the vacationers headed for that town across the state line and the farmers.

Indian Lake Road was rerouted to the east side of the line (the original roadbed is still visible near the current overpass) and a rock cut created through the Wheeler-Bassett Farm.

[3] The railroad's presence led to an old farmhouse, today known as Mutton Hill, at the southeast corner of the district, being renovated for use as country house.

It was the only one in the district until 1903 when Thomas Hidden, a recently retired New York City industrialist, bought portions of four of the old farms on Sheffield Hill Road to create his Hiddenhurst estate.

[1] Two years after Hidden's death in 1918, his estate was purchased by the Sheffield Milk Company, which combined his property with others it had acquired nearby and established a large corporate farm.

It demolished Hidden's stable and training facility and erected a large dairy complex on its site along with housing for its workers.

A new owner of the Wheeler Farm on Taylor Road around this time renovated its house to attract summer boarders, and distributed a brochure promoting it through the railroad.

The transition of the district from an insular farming community, where agriculture defined residents socially as well as economically, to one in which it was purely a business was now complete.

[4] The farm also persuaded Judge Robert W. Sweet of the Southern District of New York to void the federal listing as well, alleging violation of the Administrative Procedure Act.

A new agricultural product was added to the district in 1999, when the owners of the Manhattan coffeehouse 71 Irving Place opened a roasting facility in a former carriage house on Reagan Road.

Metro-North Railroad restored Harlem Line passenger service to a new Wassaic station, at the rail trail's southern end.

It maintains the small Coleman Station Burying Ground and the Diana K. Temple Memorial Garden along the rail trail, with native plants, trees and shrubs.